Heartbreaker
by JustPartners
Summary: Felicity Smoak is Starling City's number one heartbreaker, but what happens when she meets another Starling City heartbreaker… Oliver Queen?
1. Chapter 1

**DISCLAIMER: I don't own Arrow or the characters they belong to the CW and DC.**

 **I haven't written for a while so here is an idea that I've been toying with for a while now. Tell me what you think!**

 **Hope you Enjoy! :)**

Felicity Smoak considered herself a smart woman. She graduated at the top of her class at MIT, built a computer in second grade, and when it came to men she never got her heart broken. Ever since her father left her and her mother when she was in elementary school she vowed to never let her heart get broken by another man again. Sure she had boyfriends in the past, but she always ended it before it got too serious. Some would call her cold hearted and callous, but she just saw herself as honest and straightforward.

Tonight she was getting ready for her meeting with a potential investor. After graduating college Felicity decided to start her own computer and technology company called Smoak Enterprises. Her company specialized in creating new technology and selling it to bigger companies for mass production. Tonight she was meeting with a representative from Queen Consolidated in hopes of gaining new funding for her new computer antivirus. After checking her modest makeup one more time in the mirror she grabbed her purse and walked out her door and hailed a cab to the restaurant.

Oliver Queen hated going to these meetings for his dad. He had better things he could be doing with his time on a Friday night instead of sitting at this restaurant waiting for a computer nerd. Oliver looked down at his phone and noticed that it was only 7:15 the meeting was supposed to start at 7:30, but he showed up early in hopes of getting the meeting over with earlier so he could meet up with his best friend Tommy.

The restaurant he was at was a semi-casual restaurant. It certainly wasn't the fanciest restaurant he has eaten at, but it was more class then your everyday Big Belly Burger. Oliver looked down at his phone again and saw that only 5 minutes had passed. Sighing he put his phone back in his pocket and looked up to see a vision walk through the door. Her blonde hair was pulled up in a neat bun on top of her head and she wore a stunning dark blue dress that reached mid thigh. Oliver couldn't seem to pull his eyes away from her. She was talking to the man at the front desk with the seating arrangement and Oliver clenched his fists when he saw that the man was looking at a little bit more than just the sheet of tables.

 _What the fuck!_ Oliver thought in his head. He didn't even know this girl, _no woman she was definitely all woman,_ his said in head. He didn't even know this woman and he was already getting possessive over her, well at least he hoped to be over her tonight and maybe even under her if there was enough time. He smirked to himself as he watched her take her coat off and scan the room looking for something or someone. Her eyes stopped when she locked eyes with Oliver, and she couldn't resist a smirk of her own when she caught him looking at her.

Felicity saw Oliver Queen staring at her and to be honest she was surprised that he was here at all. Usually her meetings were with Oliver's father or with members of the tech department and Queen Consolidated. Although she had never met the younger Queen in person before you would have to live under a rock not to know who Oliver Queen was. He had the reputation of being a playboy and causing trouble throughout Starling City in his earlier years, but now he mostly worked at for his dad and "dated" a new woman every week. With a small smirk pressed against her lips she worked her way through the tables oblivious to stares she was getting from both men and women towards Oliver Queen.

When Oliver realized that the gorgeous woman making his way towards him he felt his heart stutter in his chest. For some unknown reason he was nervous he had talked to gorgeous women before and wasn't slightly nervous. He wondered if his dad would be mad at him if he decided to ditch the computer geek for sexy goddess walking towards him. Before he could make a decision he heard, "Good evening Mr. Queen."

Oliver looked up to see the woman smiling and holding her hand out to him. He quickly stood up and took her hand giving it a slight shake before planting a swift kiss on the inside of her wrist. He must have her surprised her with this because she jumped slightly when he did it.

Then he said in a husky voice, "Good evening sweetheart" and released her hand. They both stared at one another for what seemed like hours but it was actually just a couple seconds when Oliver spoke again. "You know it would be helpful to know your name, so that tonight I'll know what I'll need to be screaming." He said the last part in a low whisper that made Felicity blush and stutter out a reply.

"Uh… Mr. Queen, I'm Felicity Smoak." Oliver stared blankly at her so she clarified, "I'm here to talk about potential investments between our companies."

Oliver was having trouble picturing the woman in front of him as a computer nerd. Her voice brought him out of the haze he was in and he said, "Oh yeah! Sorry I was expecting someone a little… different. Here let me get the chair for you and please call me Oliver."

Once they both sat down Oliver was still shocked that someone like her was one of the greatest computer technicians in the country. Felicity embarrassment died down and she started talking about the benefits of Queen Consolidated investing with Smoak Enterprises. She talked about how putting a little bit of Oliver's Company into hers could lead to great business success for both parties, but Oliver wasn't paying any attention to what she was saying. Instead he watched the way her eyes would light up every time whenever she was talking about her antivirus that she created.

Halfway through her speech Felicity realized that Oliver wasn't paying any attention to what she was saying.

"Umm Oliver. Oliver. Oliver!" Oliver snapped his head up and came out of his thoughts.

"Huh?" he said when looked up to see a not very happy Felicity.

"Have you even heard a word I've said?" she said when he finally focused on her.

"Of course I have." He said somewhat defensively sitting back further in his chair.

"Alright. Tell me what I said then" Felicity said leaning forward slightly resting her elbows on the table looking at him expectantly.

"Well…" Oliver started, "You said some stuff about computers." Felicity just looked at him clearly not amused. This time Oliver leaned for on his elbows and said with a wink, "Then you talked about putting some me into some of you in order to have a successful night."

Felicity blushed bright red and sputtered at Oliver, "I didn't... I wasn't… I was talking…" Finally she regained her ability to speak and she said, "I was talking about our companies Mr. Queen."

Oliver leaned back and shrugged and said, "You say tomato. I say tomatoe."

Felicity put her head in hands and determined that she was getting nowhere with this dinner, but she was Felicity Smoak and she wasn't just going to give up. She stood up quickly. Oliver was obviously confused because he quickly stood up almost knocking his chair down.

"What's wrong?" he said sounding concerned.

Felicity simply said, "Let's go" and turned to exit the restaurant. Oliver grabbed his coat and quickly followed her. Felicity hailed a cab and told Oliver to get in. Once they were both in the cab Felicity told the driver her address and they set off towards her apartment.

Next to her Oliver was extremely confused as to what was happening. One second he was getting ready to have dinner with a beautiful woman, and now he was sitting in a cab on the way to her apartment. The cab was filled with silence, but not an uncomfortable silence. In only a few short minutes they arrived at her apartment. Felicity reached into her purse to pay, but Oliver was quicker than her and paid the driver. Felicity muttered a "thanks" and grabbed Oliver's hand leading him up to her apartment.

They took the stairs up to her apartment since she was only on the second floor and soon they were in front of her door. Oliver was getting ready to ask what they were doing there, but Felicity beat him to it. She turned away from the door to face him so that her back was to her door.

"Ok. The dinner was obviously not working. You clearly were too distracted to concentrate on my proposal or my company in general so I came up with a plan. You and I are going to have sex."

Oliver looked at her blankly and stuttered out, "Ssexx?"

Felicity looked up at him and grabbed a hold of the lapels of his jacket. "Yes sex. I assume you know what that is considering you are Oliver Queen. If not then they really do lie in all of those gossip magazines!"

Oliver looked down at her and said, "Of course I know what sex is! I'm just confused about why you suddenly decided we are going to have it!"

One of Felicity's hands left his lapel and worked its way up his button up shirt and started slowly undoing the buttons. She sighed softly and said, "Ok I'm going to explain this one more time. The dinner wasn't working, because you were too distracted. So in order to make you less distracted we are going to have sex. Then when we have another meeting to discuss our companies there won't be any distractions."

Oliver's breathing was starting to increase as Felicity slowly, so very slowly, undid his buttons so that the top part of his chest was showing for her to run her hands across. Oliver pressed her closer up against the door. His voice was a deep growl when he said, "Do you really think that is going to work?"

Felicity looked up at him and removed her hand from his lapel to the hair on the back of his head. She pulled his head down to meet hers, but before their lips could touch she said with a smirk, "Of course. Now what do you say Mr. Queen are going to sex me up or do I have to find a new company?"

Oliver closed the remaining distance and crushed his lips to hers.

 **Authors Note: Loved it? Hated it? Please review. Do I Continue or not..?**


	2. Chapter 2

**DISCLAIMER: I don't own Arrow or the characters they belong to the CW and DC.**

 **I apologize for not updating sooner. I debated continuing this story of not. Tell me what you think!**

 **Hope you Enjoy! :)**

The morning after Felicity's creative business strategy was an interesting one for Oliver. It started out good enough. He woke up to the smell of fresh coffee, but no Felicity. He pulled on his clothes from last night leaving his shirt unbuttoned, because if he remembered correctly Felicity had a thing for his abs and with them out he might even get some morning sex he thought to himself. He wondered what Felicity would think of him doing his morning workout on the salmon ladder. Oh well, maybe he can get a different type of workout this morning.

When Oliver walked out into the kitchen, however, there was still no Felicity. Walking up to the counter next to the coffee pot was a note.

 _Oliver,_

 _Had a_ _good time last night. Help yourself to some coffee._

 _~Felicity_

Oliver stared at the note. That's it he thought, just a _had a good time last night_. This had never happened to Oliver before, usually he was the one leaving vague notes in the morning. Typically he would be excited about not having to deal with a one night stand in the morning. He couldn't explain it, but for some reason he was kind of disappointed that he didn't get to see Felicity this morning. After helping himself to a cup of coffee Oliver finished getting dressed and locked Felicity's front door before pulling it closed behind him. He hailed a cab and gave the cabbie directions to his apartment so he could change before having to go to the office. Oliver was still feeling a bit annoyed about being not getting to see Felicity this morning, but then suddenly he thought of an idea. He pulled out his phone and called his father.

Across town at Smoak Enterprises Felicity sighed. Not only did she have to wake up early this morning for work she also had to leave a man who is basically a Greek god in her bed. She had to scramble to write her typical morning after note and get her glorious coffee made. Felicity's diet consisted mostly of coffee and Big Belly Burger. She wasn't afraid to leave Oliver alone in her apartment, because she has the highest security tech hooked up in every room, including cameras and security alarms. So when Felicity got to the office that morning she switched on her computer and monitored Oliver waking up and walking practically shirtless through her apartment.

 _Oh those abs_ she thought when she watched him in the kitchen reading her note. She couldn't help thinking maybe her sure fire plan from last night was going to backfire. Sure she had a fan-freaking-tastic time last night, but she's not one hundred percent certain that it did anything to help her and Oliver, at least businesswise. When Oliver left her apartment Felicity turned on her security system that armed all of her doors and windows and locked them. After that Felicity sat there sipping her coffee thinking about last night.

 _After the scorching kiss outside her door Oliver and her eventually made it inside her apartment. Once she closed the door she found her back up against it again as Oliver moved in for another kiss. This time however his hands were more mobile and found their way to the straps of her dress and slowly pulled them down, exposing more of her neck to him as he trailed kisses down her neck. Felicity shivered, but not because she was cold._

" _You cold sweetheart?" Oliver murmured against her ear and pulled his face back with a knowing smirk. Felicity took this moment to step out of her heels and as she did she also continued unbuttoning his shirt. Now Felicity was considerably shorter than Oliver and had to reach up on her tip toes to wrap her arms around his neck to bring him down for a kiss. She slowly scraped her hand through the hair on the back of his head and he gave an involuntary shiver._

" _You cold sweetheart?" she repeated his word from earlier. Before he could respond she pulled away from him and began walking down the hallway toward her room unzipping her dress as she walked. By the time she reached the doorway her dress was left forgotten in the middle of the hallway in a heap._

" _Come on Mr. Queen I'm sure we could find a way to warm up this business deal. Don't ya think?" she said over her shoulder as she continued walking into her bedroom leaving Oliver still standing by the front door in shock._

 _Oliver shook his head to get him out of his stupor and charged into the bedroom after her._

Felicity pulled herself out of the memory from the night before and looked down at her phone and noticed it was 9:20. _Frack_! She only had 10 minutes until she had to be at a meeting the actual Mr. Queen, Oliver's father, and the rest of the IT department. She quickly grabbed her stuff and power walked to the conference room.

Thankfully it appeared that she arrived before Mr. Queen the rest of the IT department. Not for the first time that day Felicity wondered if Oliver was going to come to the meeting.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~After getting off the phone with his father Oliver felt almost giddy and couldn't keep the smile off his face. He thought that it was funny that Felicity's entire plan was for them to sleep together so that they could stop thinking about sleeping with each other, but instead it had the opposite effect. Now Oliver couldn't get Felicity out of his head and he was prepared to do anything just to get her in bed with him again. If that meant joining his father's team in order to get another "meeting" with her it will definitely be worth it.

Oliver walked into Smoak Enterprises with a smirk on his face and a spring in his step in anticipation of seeing Felicity. The long ride in the elevator to the conference room made Oliver nervous and his fingers did their usual twitch of nervousness. By the time he made it to the conference room his nervous were almost enough to drive him back to the elevators. _Don't be such a pansy Queen_ he thought _you're just going to a meeting you weren't necessarily invited to just to see the woman who slept with the night before._ Totally normal situation he was about to walking into.

So far it was just Felicity and a couple of other IT members from her company on the other side of the room setting up the presentation. She looked up to see the Mr. Queen that she didn't want to see, even though she really did want to see him, walking into the conference room. _Damn he looks good in a suit_ she thought. No! This was not how her plan was supposed to work. She was supposed to sleep with him once and then they were supposed to move on and be colleagues.

"Ms. Smoak" he greeted her with a charming smile. He walked around the table in the middle of the room to shake her hand.

"Mr. Queen. I didn't know you were coming today," Felicity said shaking his hand. Oliver smiled seemed to grow as his eyes raked down her body and back up again. He pulled her in close while the IT workers were preoccupied.

"Hopefully if things go according to plan you'll be coming today too," he murmured in her ear. Felicity let out a shocked gasp and slightly blushed. Then Oliver pulled away and took his seat next to where Felicity put her stuff.

"Hey Felicity can you come help us quick?" one of the IT women said over by the projector. Felicity felt Oliver's eyes on her as she bent over to fix the projection problem. She kept sneaking glances over in Oliver's direction and he continued to look at her with a heated look that almost made her run over and take him right there in the chair meeting be damned. After finally fixing the projection problem Felicity saw Oliver's father and the rest of the people for the meeting walking into the conference room. She greeted the new comers and walked back over to her spot next to Oliver to get her laptop for the meeting. While she was bending over to pick up her stuff she subtly leaned down to Oliver's ear.

"Promises promises Mr. Queen," she said huskily and picked up her laptop and walked to the front of the conference table. With a confident smirk she said, "All right everyone let's begin…"

 **Authors Note: Loved it? Hated it? Please review. Do I Continue or not..?**


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